A Plot: While cleaning out the garage, Erica, Barry, and Adam discover a box full of love letters written by Murray to a woman named Anita, his first love. Beverly finds out and learns that her engagement ring is the same one Murray gave to his ex-fiancée.
B Plot: Adam falls for the girl next door, his cute neighbor Dana Caldwell, and turns to Pops for advice.
- Literal-Minded: When Adam tells Murray he's also having love problems, Murray replies with "tell me about it". Adam actually does try to explain before Murray clarifies it.
- "Not Making This Up" Disclaimer: The episode ends with the reveal that the real life Beverly did in fact got a used ring (and even still wears it today).
- The Scrooge: When confronted, Murray states that he reused the ring, ignoring the emotional implications, because it was incredibly expensive and he couldn't return it.
- Shout-Out: Adam finds inspiration in the romantic comedy Say Anything..., and holds up a boombox outside Dana's window to woo her, just like the character in the movie did. However, this does not go well.
- With This Ring: The A Plot centers around Beverly learning her ring was used, arguing for a new one, and then settling for the pre-owned ring after Murray shows his love.
